CN104428292B - 氨基磺酸苯基烷基酯化合物及包含所述化合物的肌肉松弛组合物 - Google Patents
氨基磺酸苯基烷基酯化合物及包含所述化合物的肌肉松弛组合物 Download PDFInfo
- Publication number
- CN104428292B CN104428292B CN201380031295.2A CN201380031295A CN104428292B CN 104428292 B CN104428292 B CN 104428292B CN 201380031295 A CN201380031295 A CN 201380031295A CN 104428292 B CN104428292 B CN 104428292B
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- China
- Prior art keywords
- base
- sulfamic acid
- methyl esters
- preparative example
- nmr
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 0 Cc1c(*)c(N)c(*=C)*(P2CC2)c1*(*)=* Chemical compound Cc1c(*)c(N)c(*=C)*(P2CC2)c1*(*)=* 0.000 description 22
- FTCQUNFKQYAVBC-RMKNXTFCSA-N CC(C)(C)C(OCC/C=C/c(cccc1)c1Cl)=O Chemical compound CC(C)(C)C(OCC/C=C/c(cccc1)c1Cl)=O FTCQUNFKQYAVBC-RMKNXTFCSA-N 0.000 description 1
- DXMISZNFGHLFFF-NSHDSACASA-N CC(C)(O)O[C@@H](CCO)c(cccc1)c1Cl Chemical compound CC(C)(O)O[C@@H](CCO)c(cccc1)c1Cl DXMISZNFGHLFFF-NSHDSACASA-N 0.000 description 1
- XPKRGYFLXOSWBC-UHFFFAOYSA-N CC(C)(OC1CCO)OC1c(cccc1)c1Cl Chemical compound CC(C)(OC1CCO)OC1c(cccc1)c1Cl XPKRGYFLXOSWBC-UHFFFAOYSA-N 0.000 description 1
- INLPMARGHPUMDP-GHMZBOCLSA-N CC(C)(O[C@@H]1CO)O[C@@H]1c1ccccc1 Chemical compound CC(C)(O[C@@H]1CO)O[C@@H]1c1ccccc1 INLPMARGHPUMDP-GHMZBOCLSA-N 0.000 description 1
- AZEZVVSDQVPSEZ-QWRGUYRKSA-N CC(C)(O[C@H]1CO)O[C@H]1c(ccc(Cl)c1)c1Cl Chemical compound CC(C)(O[C@H]1CO)O[C@H]1c(ccc(Cl)c1)c1Cl AZEZVVSDQVPSEZ-QWRGUYRKSA-N 0.000 description 1
- INLPMARGHPUMDP-QWRGUYRKSA-N CC(C)(O[C@H]1CO)O[C@H]1c1ccccc1 Chemical compound CC(C)(O[C@H]1CO)O[C@H]1c1ccccc1 INLPMARGHPUMDP-QWRGUYRKSA-N 0.000 description 1
- AMXAINKJMNCMAY-UHFFFAOYSA-N CC(C)([O-])/[O]=C/C(CCCO)Cc(cccc1)c1Cl Chemical compound CC(C)([O-])/[O]=C/C(CCCO)Cc(cccc1)c1Cl AMXAINKJMNCMAY-UHFFFAOYSA-N 0.000 description 1
- CEXUDYWONSSWTR-UHFFFAOYSA-N CC1C=CC=CC1C(CCO)C[O-]C1(CCCCC1)[O-] Chemical compound CC1C=CC=CC1C(CCO)C[O-]C1(CCCCC1)[O-] CEXUDYWONSSWTR-UHFFFAOYSA-N 0.000 description 1
- WCJFZQQDMJTAQE-YSSOQSIOSA-N CCC(CC)(OC1CCOC)O[C@@H]1c1ccccc1N Chemical compound CCC(CC)(OC1CCOC)O[C@@H]1c1ccccc1N WCJFZQQDMJTAQE-YSSOQSIOSA-N 0.000 description 1
- VEJSPIVMOGPJMU-TZHYSIJRSA-N CCC(CC)(O[C@@H]1CCOC(C(C)(C)C)=O)OC1c(cccc1)c1Cl Chemical compound CCC(CC)(O[C@@H]1CCOC(C(C)(C)C)=O)OC1c(cccc1)c1Cl VEJSPIVMOGPJMU-TZHYSIJRSA-N 0.000 description 1
- PQXCWVJPSJRHLH-CHWSQXEVSA-N CCC(CC)(O[C@@H]1CO)O[C@@H]1c(ccc(Cl)c1)c1Cl Chemical compound CCC(CC)(O[C@@H]1CO)O[C@@H]1c(ccc(Cl)c1)c1Cl PQXCWVJPSJRHLH-CHWSQXEVSA-N 0.000 description 1
- NKDDFLXBYICKCV-UONOGXRCSA-N CCC(CC)(O[C@H]1C(OCC)=O)O[C@H]1c(c(N)ccc1)c1N Chemical compound CCC(CC)(O[C@H]1C(OCC)=O)O[C@H]1c(c(N)ccc1)c1N NKDDFLXBYICKCV-UONOGXRCSA-N 0.000 description 1
- ULJAJKUCWPLHHO-KZUDCZAMSA-N CCC1(CC)O[C@@H](CO)C(Cc2ccccc2N)O1 Chemical compound CCC1(CC)O[C@@H](CO)C(Cc2ccccc2N)O1 ULJAJKUCWPLHHO-KZUDCZAMSA-N 0.000 description 1
- SIXAROFEESHMBR-BQYQJAHWSA-N CCOC(C)/C=C/c(c(Cl)ccc1)c1Cl Chemical compound CCOC(C)/C=C/c(c(Cl)ccc1)c1Cl SIXAROFEESHMBR-BQYQJAHWSA-N 0.000 description 1
- JAKOHGXFAISIIX-BMVHATROSA-N CCOC([C@H]1OC(C)O[C@@H]1c(c(Cl)ccc1)c1Cl)=O Chemical compound CCOC([C@H]1OC(C)O[C@@H]1c(c(Cl)ccc1)c1Cl)=O JAKOHGXFAISIIX-BMVHATROSA-N 0.000 description 1
- DMKUXBOMTIBNTJ-XBXARRHUSA-N COC(/C=C/Cc1ccccc1Cl)=O Chemical compound COC(/C=C/Cc1ccccc1Cl)=O DMKUXBOMTIBNTJ-XBXARRHUSA-N 0.000 description 1
- RVBQSTISRBKZTG-HWKANZROSA-N COC(/C=C/c(ccc(Cl)c1)c1Cl)=O Chemical compound COC(/C=C/c(ccc(Cl)c1)c1Cl)=O RVBQSTISRBKZTG-HWKANZROSA-N 0.000 description 1
- POTRTUQCRHOIFM-VOTSOKGWSA-N COC(/C=C/c(cccc1)c1Cl)=O Chemical compound COC(/C=C/c(cccc1)c1Cl)=O POTRTUQCRHOIFM-VOTSOKGWSA-N 0.000 description 1
- GZSQZSAQCMTAOF-UHFFFAOYSA-N COC(CCC(c1ccccc1)[O](C1(CCCC1)[O]=C)#C)=O Chemical compound COC(CCC(c1ccccc1)[O](C1(CCCC1)[O]=C)#C)=O GZSQZSAQCMTAOF-UHFFFAOYSA-N 0.000 description 1
- GRLUWXQRNMHDRW-QWHCGFSZSA-N COC([C@@H]1OC2(CCCC2)O[C@H]1c(ccc(Cl)c1)c1Cl)=O Chemical compound COC([C@@H]1OC2(CCCC2)O[C@H]1c(ccc(Cl)c1)c1Cl)=O GRLUWXQRNMHDRW-QWHCGFSZSA-N 0.000 description 1
- NVWUXRKXAGCJIQ-LSDHHAIUSA-N COC([C@@H]1OC2(CCCCC2)O[C@H]1Cc1ccccc1)=O Chemical compound COC([C@@H]1OC2(CCCCC2)O[C@H]1Cc1ccccc1)=O NVWUXRKXAGCJIQ-LSDHHAIUSA-N 0.000 description 1
- WWFRQHIJCKTGRO-CKDQBVIESA-N COC([C@H]1OC(c2ccccc2)O[C@@H]1c(cccc1)c1Cl)=O Chemical compound COC([C@H]1OC(c2ccccc2)O[C@@H]1c(cccc1)c1Cl)=O WWFRQHIJCKTGRO-CKDQBVIESA-N 0.000 description 1
- CMLVHRSXPSWEQR-MYJWUSKBSA-N COC([C@H]1OC(c2ccccc2)[O]=C1c(ccc(Cl)c1)c1Cl)=O Chemical compound COC([C@H]1OC(c2ccccc2)[O]=C1c(ccc(Cl)c1)c1Cl)=O CMLVHRSXPSWEQR-MYJWUSKBSA-N 0.000 description 1
- NPSNZGXOMWNEAS-OLZOCXBDSA-N COC([C@H]1OC2(CCCC2)O[C@@H]1c(cccc1)c1Cl)=O Chemical compound COC([C@H]1OC2(CCCC2)O[C@@H]1c(cccc1)c1Cl)=O NPSNZGXOMWNEAS-OLZOCXBDSA-N 0.000 description 1
- JTRAIVIIWQZQFD-OLZOCXBDSA-N COC([C@H]1OC2(CCCC2)O[C@@H]1c1ccccc1)=O Chemical compound COC([C@H]1OC2(CCCC2)O[C@@H]1c1ccccc1)=O JTRAIVIIWQZQFD-OLZOCXBDSA-N 0.000 description 1
- MBIVIJYFNCDYNH-KGLIPLIRSA-N COC([C@H]1OC2(CCCCC2)O[C@@H]1c(ccc(Cl)c1)c1Cl)=O Chemical compound COC([C@H]1OC2(CCCCC2)O[C@@H]1c(ccc(Cl)c1)c1Cl)=O MBIVIJYFNCDYNH-KGLIPLIRSA-N 0.000 description 1
- XVGCOXCRKZSMLB-KGLIPLIRSA-N Cc1c([C@H]2OC3(CCCC3)O[C@@H]2C(OC)=O)cccc1 Chemical compound Cc1c([C@H]2OC3(CCCC3)O[C@@H]2C(OC)=O)cccc1 XVGCOXCRKZSMLB-KGLIPLIRSA-N 0.000 description 1
- BBUHAKFAFBXHQI-SWQDIRLTSA-N Cc1ccccc1[C@@H]1OC(c2ccccc2)O[C@H]1C(OC)=O Chemical compound Cc1ccccc1[C@@H]1OC(c2ccccc2)O[C@H]1C(OC)=O BBUHAKFAFBXHQI-SWQDIRLTSA-N 0.000 description 1
- RKZADVTZFIMSER-DUXPYHPUSA-N OC(C/C=C/Cc(cccc1)c1Cl)=O Chemical compound OC(C/C=C/Cc(cccc1)c1Cl)=O RKZADVTZFIMSER-DUXPYHPUSA-N 0.000 description 1
- JBTQGRWNBPRZAQ-ZDUSSCGKSA-N OCC1=[O]C2(CCCC2)O[C@@H]1c(c(Cl)ccc1)c1Cl Chemical compound OCC1=[O]C2(CCCC2)O[C@@H]1c(c(Cl)ccc1)c1Cl JBTQGRWNBPRZAQ-ZDUSSCGKSA-N 0.000 description 1
- HYWYETUJJJVVSF-HOTGVXAUSA-N OCC[C@@H]1OC2(CCCCC2)O[C@H]1Cc1ccccc1 Chemical compound OCC[C@@H]1OC2(CCCCC2)O[C@H]1Cc1ccccc1 HYWYETUJJJVVSF-HOTGVXAUSA-N 0.000 description 1
- SVMCLMGRZYECJA-JKSUJKDBSA-N OCC[C@@H]1[C@@H](Cc2ccccc2)OC2(CCCC2)C1 Chemical compound OCC[C@@H]1[C@@H](Cc2ccccc2)OC2(CCCC2)C1 SVMCLMGRZYECJA-JKSUJKDBSA-N 0.000 description 1
- HSMPKPYUYMUWTQ-GVJPCGBOSA-N OC[C@@H]1OC(c2ccccc2)O[C@H]1c(c(Cl)ccc1)c1Cl Chemical compound OC[C@@H]1OC(c2ccccc2)O[C@H]1c(c(Cl)ccc1)c1Cl HSMPKPYUYMUWTQ-GVJPCGBOSA-N 0.000 description 1
- YGVFXSFQDFUWJG-KSCSMHSMSA-N OC[C@@H]1OC(c2ccccc2)O[C@H]1c(cccc1)c1Cl Chemical compound OC[C@@H]1OC(c2ccccc2)O[C@H]1c(cccc1)c1Cl YGVFXSFQDFUWJG-KSCSMHSMSA-N 0.000 description 1
- KSSNLJRNUGGBMY-WCQYABFASA-N OC[C@@H]1OC2(CCCC2)O[C@H]1c(c(Cl)ccc1)c1Cl Chemical compound OC[C@@H]1OC2(CCCC2)O[C@H]1c(c(Cl)ccc1)c1Cl KSSNLJRNUGGBMY-WCQYABFASA-N 0.000 description 1
- ABDDWFNICDXWHJ-CHWSQXEVSA-N [O-][N+](c1c([C@H]2OC3(CCCC3)O[C@@H]2CO)cccc1)=O Chemical compound [O-][N+](c1c([C@H]2OC3(CCCC3)O[C@@H]2CO)cccc1)=O ABDDWFNICDXWHJ-CHWSQXEVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261660064P | 2012-06-15 | 2012-06-15 | |
| US61/660,064 | 2012-06-15 | ||
| PCT/KR2013/005279 WO2013187727A1 (en) | 2012-06-15 | 2013-06-14 | Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104428292A CN104428292A (zh) | 2015-03-18 |
| CN104428292B true CN104428292B (zh) | 2017-02-08 |
Family
ID=49758484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380031295.2A Active CN104428292B (zh) | 2012-06-15 | 2013-06-14 | 氨基磺酸苯基烷基酯化合物及包含所述化合物的肌肉松弛组合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9221783B2 (enExample) |
| EP (1) | EP2861571B1 (enExample) |
| JP (1) | JP6001168B2 (enExample) |
| KR (1) | KR101699145B1 (enExample) |
| CN (1) | CN104428292B (enExample) |
| BR (1) | BR112014031396B1 (enExample) |
| CA (1) | CA2874988C (enExample) |
| ES (1) | ES2635067T3 (enExample) |
| WO (1) | WO2013187727A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015088272A1 (en) | 2013-12-12 | 2015-06-18 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compounds for use in treating or alleviating pain |
| US9937145B2 (en) * | 2013-12-12 | 2018-04-10 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compound for use in preventing or treating epilepsy |
| ES2704928T3 (es) | 2013-12-12 | 2019-03-20 | Bio Pharm Solutions Co Ltd | Compuestos derivados de sulfamato para su uso en el tratamiento o alivio del dolor |
| US11896593B2 (en) * | 2020-09-10 | 2024-02-13 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compounds for use in treating or alleviating a psychiatric disorder |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4591601A (en) * | 1985-04-12 | 1986-05-27 | Mcneilab, Inc. | Anticonvulsant dioxolane methane sulfamates |
| US4792569A (en) * | 1987-08-27 | 1988-12-20 | Mcneilab, Inc. | Anticonvulsant phenethyl sulfamates |
| US5025031A (en) * | 1989-11-30 | 1991-06-18 | A. H. Robins Co., Inc. | Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US459160A (en) * | 1891-09-08 | Half to isaac l | ||
| US2884444A (en) | 1956-01-13 | 1959-04-28 | Carter Prod Inc | 2-phenyl-1,3 propane diol dicarbamate |
| US2937119A (en) | 1959-06-11 | 1960-05-17 | Carter Prod Inc | Nu-monosubstituted-2, 2-dialkyl-1, 3-propanediol dicarbamates |
| US3313692A (en) | 1958-04-21 | 1967-04-11 | Armour Pharma | Method of inducing calming and muscle relaxation with carbamates |
| US3265727A (en) | 1962-06-26 | 1966-08-09 | Armour Pharma | Phenyl alkyl-1, 2 dicarbamates |
| JPH05140144A (ja) * | 1991-11-14 | 1993-06-08 | Nitto Denko Corp | 新規なアルコール及びその製法、及び新規なエステル並びにこの新規なアルコールからニンジン類の発根誘起物質を製造する方法 |
| JPH07228549A (ja) * | 1994-02-17 | 1995-08-29 | Japan Tobacco Inc | 新規な４−アリール−２，３−ジヒドロキシ酪酸誘導体及びその製造方法 |
| JP4145492B2 (ja) * | 1998-09-23 | 2008-09-03 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | テトラヒドロピリドエーテル |
| IS7839A (is) * | 2002-11-22 | 2004-05-23 | Merck Frosst Canada Ltd. | 4-oxó-1-(3-setið fenýl-1,4-díhýdró-1,8-naftýridín-3-karboxamíð fosfódíesterasa-4 hindrar |
| US20050192286A1 (en) | 2003-10-22 | 2005-09-01 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
| WO2007005935A2 (en) * | 2005-07-06 | 2007-01-11 | Molecular Neuroimaging, Llc | Norepinephrine transporter radiotracers and methods of syntheses thereof |
| EP1945651B1 (en) * | 2005-10-25 | 2014-06-25 | The Ludwig Institute for Cancer Research | Analogs of alpha galactosylceramide and uses thereof |
-
2013
- 2013-06-14 JP JP2015517189A patent/JP6001168B2/ja active Active
- 2013-06-14 EP EP13803704.9A patent/EP2861571B1/en active Active
- 2013-06-14 BR BR112014031396A patent/BR112014031396B1/pt active IP Right Grant
- 2013-06-14 KR KR1020147035195A patent/KR101699145B1/ko active Active
- 2013-06-14 ES ES13803704.9T patent/ES2635067T3/es active Active
- 2013-06-14 CA CA2874988A patent/CA2874988C/en active Active
- 2013-06-14 CN CN201380031295.2A patent/CN104428292B/zh active Active
- 2013-06-14 WO PCT/KR2013/005279 patent/WO2013187727A1/en not_active Ceased
- 2013-06-14 US US14/401,990 patent/US9221783B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4591601A (en) * | 1985-04-12 | 1986-05-27 | Mcneilab, Inc. | Anticonvulsant dioxolane methane sulfamates |
| US4792569A (en) * | 1987-08-27 | 1988-12-20 | Mcneilab, Inc. | Anticonvulsant phenethyl sulfamates |
| US5025031A (en) * | 1989-11-30 | 1991-06-18 | A. H. Robins Co., Inc. | Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants |
Also Published As
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| EP2861571A1 (en) | 2015-04-22 |
| EP2861571A4 (en) | 2015-11-04 |
| BR112014031396B1 (pt) | 2019-11-26 |
| BR112014031396A2 (pt) | 2017-06-27 |
| EP2861571B1 (en) | 2017-05-03 |
| CA2874988C (en) | 2016-05-24 |
| JP2015531746A (ja) | 2015-11-05 |
| CN104428292A (zh) | 2015-03-18 |
| JP6001168B2 (ja) | 2016-10-05 |
| KR20150023393A (ko) | 2015-03-05 |
| US20150266848A1 (en) | 2015-09-24 |
| US9221783B2 (en) | 2015-12-29 |
| ES2635067T3 (es) | 2017-10-02 |
| KR101699145B1 (ko) | 2017-02-03 |
| WO2013187727A1 (en) | 2013-12-19 |
| CA2874988A1 (en) | 2013-12-19 |
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